US8796366B2 - Easily dispersible solid pigment preparations - Google Patents

Easily dispersible solid pigment preparations Download PDF

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Publication number
US8796366B2
US8796366B2 US13/146,740 US201013146740A US8796366B2 US 8796366 B2 US8796366 B2 US 8796366B2 US 201013146740 A US201013146740 A US 201013146740A US 8796366 B2 US8796366 B2 US 8796366B2
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pigment
pigment preparation
mol
structural unit
solid
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US20110288209A1 (en
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Dietmar Beck
Uwe Bechtold
Bjoern Fechner
Jesus Pitarch-Lopez
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Clariant International Ltd
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Clariant Finance BVI Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001Post-treatment of organic pigments or dyes
    • C09B67/0004Coated particulate pigments or dyes
    • C09B67/0008Coated particulate pigments or dyes with organic coatings
    • C09B67/0013Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006Preparation of organic pigments
    • C09B67/0063Preparation of organic pigments of organic pigments with only macromolecular substances
    • C09B67/0064Preparation of organic pigments of organic pigments with only macromolecular substances of phthalocynanines with only macromolecular substances
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/07Aldehydes; Ketones
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001Post-treatment of organic pigments or dyes
    • C09B67/0002Grinding; Milling with solid grinding or milling assistants
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084Dispersions of dyes
    • C09B67/0085Non common dispersing agents
    • C09B67/009Non common dispersing agents polymeric dispersing agent
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092Dyes in solid form
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B68/00Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/42Ionic groups, e.g. free acid
    • C09B68/425Anionic groups
    • C09B68/4253Sulfonic acid groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04Homopolymers or copolymers of esters
    • C09D133/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00Pigment pastes, e.g. for mixing in paints
    • C09D17/003Pigment pastes, e.g. for mixing in paints containing an organic pigment
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/45Anti-settling agents
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432Six-membered rings
    • C08K5/3437Six-membered rings condensed with carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • C08L33/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10Homopolymers or copolymers of methacrylic acid esters
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/02Printing inks
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02Emulsion paints including aerosols
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08722Polyvinylalcohols; Polyallylalcohols; Polyvinylethers; Polyvinylaldehydes; Polyvinylketones; Polyvinylketals
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/09Colouring agents for toner particles
    • G03G9/0906Organic dyes
    • G03G9/091Azo dyes

Definitions

  • the present invention relates to solid pigment preparations comprising dispersing additives based on water-soluble polymers comprising sulfonate groups and to the use of said solid pigment preparations for coloring natural and synthetic materials.
  • pigments are incorporated in a liquid phase in combination with dispersing and wetting agents through the use of energy-intensive ball mills, stirred media mills or high-performance bead mills.
  • One way to make the pigmentation of paint systems, printing inks and finishes more efficient and less cost and energy intensive consists in using easily dispersible solid pigment preparations which can be incorporated in the application system with significantly lower energy input and faster color development then conventional pigments, which is of substantial economic advantage.
  • WO 2004/046251 describes solid pigment preparations comprising water-soluble anionic additives based on homo- and copolymers of ethylenically unsaturated mono- and/or dicarboxylic acids.
  • W02004/074383 discloses solid pigment preparations which are only easily dispersible in solvent-containing application media.
  • EP-A1-1 132 434 discloses the production of easily dispersible pigment preparations by using dispersants based on aromatic polyalkylene glycols. These preparations are only compatible with aqueous application systems.
  • the solid pigment preparations described in WO 2007/039603 provide an improvement regarding compatibility in application media differing in polarity.
  • the dispersing additives used for producing such pigment preparations consist of a polymeric backbone synthesized by chain reaction and bearing side chains based on hydrophilic polyethers.
  • the reaction product of a styrene-maleic anhydride copolymer with a polyether amine is mentioned as an example of such dispersing additives.
  • Dispersion in very hydrophobic finish systems, such as solventborne industrial finishes based on long oil alkyd resins for example, is not sufficient.
  • US 2006/0142416 discloses dispersible colorants consisting of pigments and copolymers having a sulfonate group content at the pigment surface of above 100 ⁇ mol/g, for exclusively aqueous inkjet inks. These dispersible colorants are manufactured using a costly and inconvenient method, however. First, the pigment has to be dispersed using dispersant auxiliaries and high energy input and then monomers are added to the pigment dispersion and polymerized for several hours. The colorants are isolated after several centrifugation and washing steps.
  • pigment preparations with easy dispersibility in both aqueous and solvent-containing application media.
  • Such pigment preparations shall be universally compatible and their incorporation shall take place easily and without additional steps irrespective of the application medium.
  • Easily dispersible is to be understood as meaning that the pigment is incorporable in the application system with very low energy input and intensive and rapid color development.
  • gentle shearing forces for example the action of a dissolver (saw-tooth stirrer), shall be sufficient to achieve complete dispersal of the pigment, removing the need for any further cost-intensive dispersing steps.
  • the present invention provides solid pigment preparations comprising
  • R 1 , R 4 , R 6 and R 8 are each independently hydrogen or C 1 -C 4 -alkyl
  • R 2 is a covalent bond, C 1 -C 4 -alkylene, C 1 -C 4 -alkylene-C 6 -C 12 -arylene, C 6 -C 30 -arylene or the radical
  • R 3 is hydrogen, Na + , K ⁇ or N(R 1 ) 4 + ,
  • R 5 and R 7 are each independently linear or branched C 1 -C 40 -alkyl, C 5 -C 30 cycloalkyl, C 1 -C 4 -alkylene-C 6 -C 12 -aryl or C 6 -C 33 -aryl, and
  • R 9 is hydrogen, linear or branched C 1 -C 40 -alkyl, C 5 -C 30 -cycloalkyl, C 6 -C 30 -aryl, C 1 -C 4 -alkylene-C 6 -C 12 -aryl, —F, —Cl, —Br, —OH or —CN,
  • aryl may be substituted with C 1 -C 4 -alkyl groups
  • (C) from 0% to 30% by weight and preferably from 0.1% to 10% by weight of an auxiliary from the group consisting of fillers, flame retardants, preservatives, photoprotectants, pigmentary and nonpigmentary dispersants, surfactants, antioxidants, defoamers, resins and antistats,
  • an auxiliary from the group consisting of fillers, flame retardants, preservatives, photoprotectants, pigmentary and nonpigmentary dispersants, surfactants, antioxidants, defoamers, resins and antistats,
  • the pigment particles advantageously have a d 50 value between 50 and 500 nm and preferably between 70 and 350 nm.
  • the structural unit B1 derives from ethylenically unsaturated sulfonic acids of the general formula (b1).
  • the structural unit B3 derives from vinyl esters of the general formula (b3).
  • the structural unit B4 derives from the olefins of the general formula (b4).
  • the copolymers may be statistical, alternating, gradientlike or blocklike in construction.
  • the copolymers are preferably statistical in construction.
  • the average molecular weight Mw is in the range from 1000 to 50 000 g/mol. In the particularly preferred form of the copolymer, the average molecular weight Mw is in the range from 3000 to 20 000 g/mol.
  • customary surfactants which may be included as component (C) in the pigment preparations of the present invention are:
  • soy lecithin and also condensation products of fatty acid and taurine or hydroxyethanesulfonic acid similarly alkoxylation products of alkylphenols, castor oil rosin esters, fatty alcohols, fatty amines, fatty acids and fatty acid amides
  • these alkoxylation products can be equipped with ionic end groups, for example as sulfosuccinic monoesters or else as sulfonic, sulfuric and phosphoric esters, and also their salts, the sulfonates, sulfates or phosphates.
  • alkoxylated addition compounds obtained by reaction of polyepoxides with amines or bisphenol A or bisphenol A derivatives with amines, and also urea derivatives.
  • the present invention further provides a process for producing the solid pigment preparations described above, which comprises a pigment in the form of powder, granulate or press cake being mixed with at least one water-soluble dispersing additive (B) and optionally said customary auxiliaries in the presence of water or an organic solvent or a mixture of water and organic solvent and subsequently isolated in solid form.
  • B water-soluble dispersing additive
  • the pigment suspension thus obtained can be subjected to a finishing operation.
  • the finishing operation is advantageously carried out in the existing organic solvent, water or water-solvent mixture at a temperature of 50 to 250° C., particularly 70 to 200° C., especially 100 to 190° C., and advantageously for a period in the range from 5 minutes to 24 hours, particularly 5 minutes to 18 hours, especially 5 minutes to 6 hours.
  • the finishing operation is preferably carried out at the boiling temperature, especially at temperatures above the boiling point of the solvent system under superatmospheric pressure.
  • any solvent used can be removed by means of a steam distillation.
  • the pigment preparations according to the present invention are isolated in solid form, for example by filtration, decanting, centrifugation, spray drying, fluidized bed drying, belt drying, spray granulation or drying in a paddle dryer.
  • the pigment preparations according to the present invention are preferably isolated by filtration and final drying.
  • the pigment preparation obtained has a coarse particle size, it is advantageously additionally subjected to a grinding operation, dry grinding for example.
  • High molecular weight organic materials include for example cellulose ethers and esters, such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as addition polymerization resins or condensation resins, for example aminoplasts, in particular urea- and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenoplasts, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic esters, polyamides, polyurethanes or polyesters, rubber, caseine, latices, silicone, silicone resins, individually or mixed.
  • cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate
  • natural resins or synthetic resins such as addition polymerization resins or condensation resins, for example aminoplasts, in particular urea
  • the pigment preparations of the present invention are further useful in the manufacture of inkjet inks, for example on an aqueous or nonaqueous basis (“solvent-based”), microemulsion inks, UV-curable inks as well as those inks as function according to the hotmelt process for use in all conventional inkjet printers, in particular for those which are based on the bubble jet or piezo process.
  • solvent-based aqueous or nonaqueous basis
  • microemulsion inks microemulsion inks
  • UV-curable inks as well as those inks as function according to the hotmelt process for use in all conventional inkjet printers, in particular for those which are based on the bubble jet or piezo process.
  • These inks can be used to print paper but also natural or synthetic fiber materials, foils, and plastics.
  • the mixture was subjected to pressure finishing at 125° C. for 3 hours.
  • the isobutanol was then distilled off by steam distillation, the coated pigment was filtered off and washed with water to a conductivity (filtrate) ⁇ 0.5 mS/cm.
  • the coated pigment was dried in a circulating drying cabinet at 80° C. and subsequently pulverized to obtain 173 g of solid pigment preparation having 87 ⁇ mol of sulfonate groups/g of pigment preparation.
  • a dissolver equipped with a 4 cm toothed disk was used to disperse 15.0 g of the easily dispersible pigment preparations of examples 1 and 2 (or rather 9.6 g in the case of example 3) in 45.0 g (or rather 50.4 g in the case of example 3) of the long oil alkyd resin grind varnish (40%) for 30 min at 40° C. and 10 000 rpm.
  • 10 g of this pigmented grind varnish were admixed at room temperature with 10 g of a letdown mix (54%) and 30 g (or rather 20 g in the case of example 3) of a clearcoat mix by slowly stirring with a glass rod.
  • a dissolver equipped with a 4 cm toothed disk was used to disperse 36.0 g of the easily dispersible pigment preparation of examples 1 to 3 in 44.0 g of a grind mix for 30 min at 20° C. and 8000 rpm (45% millbase).
  • To prepare the white reduction 1.16 g of the millbase were homogenized with 50.84 g of waterborne white dispersion (20% of TiO 2 ) by simple manual stirring (1% white reduction).
  • the paints thus produced were drawn down as a 200 ⁇ m film on test card and dried at room temperature for 60 min.
  • the pigment in the form alternatively of powder, granulate or presscake, was pasted up in deionized water together with the dispersant and the other adjuvants and then homogenized and predispersed using a dissolver (for example from VMA-Getzmann GmbH, type AE3-M1) or some other suitable apparatus.
  • Viscosity was determined using a cone-and-plate viscometer (Roto Visco 1) from Haake at 20° C. (titanium cone: 60 mm, 1°), the relationship between viscosity and shear rate in a range between 0 and 200 s-1 being investigated. Viscosities were measured at a shear rate of 60 s-1.
  • the pigment formulation After drying, the pigment formulation has the following composition, neglecting a residual water content of about 1%:
  • the pigment formulation has high color strength in white dispersion and in lacquer, and is stable.
  • the rub-out test shows no color strength differences compared with the rubbed area.
  • the dry powder is spontaneously dispersible in the waterborne white dispersion and solventborne lacquer by manual stirring for 3 minutes, Both color systems give high color strength and also a nonflocculating application free of specks.
  • the rub-out test does not show any color strength differences compared with the rubbed area.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
US13/146,740 2009-02-12 2010-01-07 Easily dispersible solid pigment preparations Expired - Fee Related US8796366B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102009008740A DE102009008740A1 (de) 2009-02-12 2009-02-12 Leicht dispergierbare feste Pigmentzubereitungen
DE102009008740 2009-02-12
DE102009008740.0 2009-02-12
PCT/EP2010/000024 WO2010091766A1 (fr) 2009-02-12 2010-01-07 Préparations de pigment solide facilement dispersibles

Publications (2)

Publication Number Publication Date
US20110288209A1 US20110288209A1 (en) 2011-11-24
US8796366B2 true US8796366B2 (en) 2014-08-05

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US (1) US8796366B2 (fr)
EP (1) EP2396371B1 (fr)
JP (1) JP2012517511A (fr)
CN (1) CN102272236B (fr)
CA (1) CA2752185A1 (fr)
DE (1) DE102009008740A1 (fr)
ES (1) ES2406155T3 (fr)
WO (1) WO2010091766A1 (fr)

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DE102008021511A1 (de) 2008-04-30 2009-11-05 Clariant International Limited Pigmentdispergatoren und leicht dispergierbare feste Pigmentzubereitungen
CN102532939B (zh) * 2011-12-16 2014-11-12 江南大学 一种水性自分散纳米有机颜料粉体的制备方法
RU2014139009A (ru) * 2012-02-29 2016-04-20 Кэнон Кабусики Кайся Черный тонер, содержащий соединение, имеющее азокаркас
WO2015051515A1 (fr) * 2013-10-10 2015-04-16 Rohm And Haas Company Composition de liant et composition de revêtement préparée à partir de celle-ci
WO2019020157A1 (fr) * 2017-07-24 2019-01-31 Wacker Chemie Ag Composition de poudre dispersible contenant un copolymère d'alcool vinylique
WO2019020156A1 (fr) 2017-07-24 2019-01-31 Wacker Chemie Ag Copolymères d'alcool vinylique hydrophobes et solubles dans l'eau froide
EP3757178B1 (fr) * 2019-06-25 2021-09-08 Flooring Technologies Ltd. Procédé de fabrication d'au moins un matériau porteur pourvu d'un decor imprimé
CN112724706B (zh) * 2021-01-27 2023-06-13 宇虹颜料股份有限公司 一种在塑料中易分散的有机颜料制备方法

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1595680A1 (de) 1966-09-16 1970-04-23 Bayer Ag Sulfonsaeuregruppen enthaltende Polymerisate
DE2638946A1 (de) 1976-08-28 1978-03-02 Hoechst Ag Pigmentdispersionen fuer den einsatz in hydrophilen und hydrophoben medien
GB2014326A (en) 1978-02-13 1979-08-22 American Cyanamid Co Electrochromic device
US4309327A (en) * 1979-03-01 1982-01-05 Nippon Paint Co., Ltd. Polymeric resin from ethylenic amino, sulfonic monomers
EP0796876A1 (fr) 1996-03-22 1997-09-24 National Starch and Chemical Investment Holding Corporation Compositions de colorants et méthodes pour leur préparation
EP1132434A2 (fr) 2000-03-03 2001-09-12 Bayer Corporation Procédé de préparation de pigments organiques
WO2004046251A2 (fr) 2002-11-18 2004-06-03 Basf Aktiengesellschaft Preparations de pigment solides, contenant des additifs tensioactifs anioniques hydrosolubles renfermant des groupes carboxylate
WO2004074383A2 (fr) 2003-02-20 2004-09-02 Ciba Specialty Chemicals Holding Inc. Composition pigmentaire dispersee par agitation
DE102004032399A1 (de) 2004-07-03 2006-02-09 Construction Research & Technology Gmbh Mischungszusammensetzung enthaltend Copolymere auf Basis von ungesättigten Carbonsäure- und Alkenylether-Derivaten sowie sulfogruppenhaltige Co- und Terpolymere
US20060047062A1 (en) 2004-08-26 2006-03-02 Hsu Shui-Jen R Coating compositions having improved stability
US20060142416A1 (en) * 2004-06-22 2006-06-29 Canon Kabushiki Kaisha Dispersible colorant and manufacturing method thereof, aqueous ink using the same, ink tank, ink-jet recording apparatus, ink-jet recording method, and ink-jet recording image
WO2007039603A2 (fr) 2005-10-04 2007-04-12 Akzo Nobel Coatings International B.V. Preparation de pigment
US20110046274A1 (en) 2008-04-30 2011-02-24 Clariant Finance (Bvi) Limited Pigment Disperser And Easily Dispersed Solid Pigment Preparations

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2913719B2 (ja) * 1990-01-12 1999-06-28 東亞合成株式会社 分散剤
JP3009089B2 (ja) * 1994-03-09 2000-02-14 大日精化工業株式会社 湿粉状顔料組成物及びその製造方法
IN220164B (fr) * 1997-09-08 2008-07-11 Ciba Geigy Ag
JP2002206013A (ja) * 2000-11-09 2002-07-26 Kansai Paint Co Ltd 顔料分散樹脂及びこの樹脂を含有する水性顔料分散体
JP3967949B2 (ja) * 2001-04-05 2007-08-29 関西ペイント株式会社 顔料分散用樹脂
JP4084028B2 (ja) * 2001-11-07 2008-04-30 大日精化工業株式会社 液体現像剤用顔料組成物、顔料分散液及びそれらの製造方法
JP4029621B2 (ja) * 2002-01-29 2008-01-09 東洋インキ製造株式会社 顔料組成物および顔料分散体
JP2008239994A (ja) * 2002-04-16 2008-10-09 Toyo Ink Mfg Co Ltd インクジェットインキおよびカラーフィルタ
JP4314869B2 (ja) * 2002-04-16 2009-08-19 東洋インキ製造株式会社 インクジェットインキおよびカラーフィルタ
JP2004122574A (ja) * 2002-10-02 2004-04-22 Konica Minolta Holdings Inc インクジェット記録方法
JP2006299239A (ja) * 2005-03-22 2006-11-02 Kansai Paint Co Ltd 顔料調製物及びそれを含んでなる塗料組成物

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1595680A1 (de) 1966-09-16 1970-04-23 Bayer Ag Sulfonsaeuregruppen enthaltende Polymerisate
US3547899A (en) * 1966-09-16 1970-12-15 Bayer Ag Polymers containing sulphonic acid groups
DE2638946A1 (de) 1976-08-28 1978-03-02 Hoechst Ag Pigmentdispersionen fuer den einsatz in hydrophilen und hydrophoben medien
US4156616A (en) 1976-08-28 1979-05-29 Hoechst Aktiengesellschaft Pigment dispersion for use in hydrophilic and hydrophobic media
GB2014326A (en) 1978-02-13 1979-08-22 American Cyanamid Co Electrochromic device
US4309327A (en) * 1979-03-01 1982-01-05 Nippon Paint Co., Ltd. Polymeric resin from ethylenic amino, sulfonic monomers
EP0796876A1 (fr) 1996-03-22 1997-09-24 National Starch and Chemical Investment Holding Corporation Compositions de colorants et méthodes pour leur préparation
EP1132434A2 (fr) 2000-03-03 2001-09-12 Bayer Corporation Procédé de préparation de pigments organiques
US20060000392A1 (en) 2002-11-18 2006-01-05 Basf Akitiengesellschaft Solid pigment preparations containing water-soluble anionic surface-active additives that comprise carboxylate groups
WO2004046251A2 (fr) 2002-11-18 2004-06-03 Basf Aktiengesellschaft Preparations de pigment solides, contenant des additifs tensioactifs anioniques hydrosolubles renfermant des groupes carboxylate
US8124672B2 (en) 2002-11-18 2012-02-28 Basf Aktiengesellschaft Solid pigment preparations containing water-soluble anionic surface-active additives that comprise carboxylate groups
WO2004074383A2 (fr) 2003-02-20 2004-09-02 Ciba Specialty Chemicals Holding Inc. Composition pigmentaire dispersee par agitation
US20060142416A1 (en) * 2004-06-22 2006-06-29 Canon Kabushiki Kaisha Dispersible colorant and manufacturing method thereof, aqueous ink using the same, ink tank, ink-jet recording apparatus, ink-jet recording method, and ink-jet recording image
DE102004032399A1 (de) 2004-07-03 2006-02-09 Construction Research & Technology Gmbh Mischungszusammensetzung enthaltend Copolymere auf Basis von ungesättigten Carbonsäure- und Alkenylether-Derivaten sowie sulfogruppenhaltige Co- und Terpolymere
US20070287817A1 (en) 2004-07-03 2007-12-13 Markus Maier Mixture Composition Containing Unsaturated Carboxylic Acid and Alkene Ether Derivative Based Copolymers and Copolymers and Terpolymers Containing Sulfo Groups and Use Thereof
US20110218289A1 (en) 2004-07-03 2011-09-08 Markus Maier Mixture composition containing copolymers based on unsaturated carboxylic acid and alkenyl ether derivatives and copolymers and terpolymers containing sulfo groups and use thereof
US20060047062A1 (en) 2004-08-26 2006-03-02 Hsu Shui-Jen R Coating compositions having improved stability
WO2007039603A2 (fr) 2005-10-04 2007-04-12 Akzo Nobel Coatings International B.V. Preparation de pigment
US20090030139A1 (en) 2005-10-04 2009-01-29 Akzo Nobel Coatings International B.V. Pigment preparation
US7842757B2 (en) 2005-10-04 2010-11-30 Akzo Nobel Coatings International B.V. Pigment preparation
US20110046274A1 (en) 2008-04-30 2011-02-24 Clariant Finance (Bvi) Limited Pigment Disperser And Easily Dispersed Solid Pigment Preparations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
PCT International Preliminary Report on Patentability for PCT/EP 2010/000024, mailed Aug. 16, 2011.
PCT International Search Report for PCT/EP 2010/000024, mailed Jul. 13, 2010.
Yotaro, "Self-Assembling Amphiphilic Polyelectrolytes and their Nanostructures" Chinese Journal of Polymer Science Zhongguo Huakuehui, CN, vol. 18, No. 40; pp. 323-336, XP 009107054 (Jan. 1, 2000).

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EP2396371A1 (fr) 2011-12-21
CN102272236B (zh) 2013-12-04
DE102009008740A1 (de) 2010-08-19
CA2752185A1 (fr) 2010-08-19
US20110288209A1 (en) 2011-11-24
CN102272236A (zh) 2011-12-07
ES2406155T3 (es) 2013-06-05

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